Rude made his WWF debut in July 1987 as the newest addition to the Bobby Heenan Family. His first feud in the WWF was with Heenan's former muscle bound charge "Mr. Wonderful" Paul Orndorff (who Heenan had dropped after Rude joined the Family), before starting one of his most famous feuds with Jake "The Snake" Roberts.[15] Rude had a routine where, before the match, he would make a show of removing his robe while insulting the males in the crowd (usually calling them "Fat", "out of shape" or "sweathogs") and, after his victories, he would kiss a woman that Heenan picked from the fans.[10] One of Rude's trademarks was his specially airbrushed tights that he wore during matches. In one storyline, he tried to get Roberts' real-life wife, Cheryl, to comply (though not knowing when Heenan chose her that she was in fact the wife of Jake "The Snake"). After Mrs Roberts rejected him and revealed who she was there to see, Rude got angry (after she slapped him) and grabbed her wrist, berating her on the microphone when Roberts ran from the dressing room to make the save.[10] On another occasion during the Roberts/Rude feud, Rude came to the ring with a picture of Cheryl stenciled on the front of his tights. A furious Roberts charged the ring and stripped Rude, appearing to television viewers to leave him naked,[16] although the live audience saw him stripped to a g-string instead.

Through mid-1988 Rude continued to wear a second pair of tights under the one he wore to the ring, including during his match against the Junk Yard Dog at the inauguralSummerSlam at Madison Square Garden. During the match Rude had the JYD on his back and had climbed to the top turnbuckle. While up there he pulled down his tights to reveal a second with Cheryl Roberts printed on them. After hitting the Dog with a flying fist, he was attacked by Roberts who had seen the action from the dressing room. Roberts attack on Rude caused the JYD to be disqualified, giving Rude the win. Rude's feud with Roberts came to its conclusion when Roberts pinned Rude following a DDT during the 1988 Survivor Series.

In 1992, Rude and Madusa left The Dangerous Alliance and feuded with Nikita Koloff. Rude challenged reigning WCW World Heavyweight ChampionRon Simmons on several occasions but did not defeat him. In December 1992, Rude suffered a legitimate injury and was forced to forfeit the United States Championship, thus ending his reign of nearly 14 months, a reign that still stands today as the second longest reign in the almost 40 year history of the title.[10] Rude returned alone in April 1993 and tried to reclaim the title from Dustin Rhodes, who had won it while he was injured. The title was eventually held up after several controversial finishes to matches between the two; although, Rhodes regained the title in a rematch.[23]

Rude switched his sights to the NWA World Heavyweight Championship, making his intentions clear on August 28, 1993, when he was the guest on then-champion Ric Flair's "A Flair For the Gold" talk segment.[11] Rude defeated Flair for the title in September 1993 at Fall Brawl.[24] As WCW had recently withdrawn from the NWA, WCW lost the rights to continue using the NWA World Heavyweight Championship. WCW created their own championship, dubbing it the WCW International World Heavyweight Championship, which Rude lost to Hiroshi Hase on March 16, 1994 in Tokyo, Japan.[24] Rude regained the title just eight days later in Kyoto, Japan.[24] After dropping the title to Sting on April 17, Rude pinned Sting on May 1 in Fukuoka to become a three-time champion.[24] Rude, however, injured his back during the match when, upon receiving a suicide dive at ringside, he landed on the corner of the raised platform surrounding the ring; unable to wrestle, he was stripped of the title (with the storyline excuse that he was found to have used the title belt as a weapon in the course of the match).[10][24] Rude retired shortly thereafter.[10]

On August 11, 1997, Rude returned to WWF as the "insurance policy" of the D-Generation X (DX) stable (Shawn Michaels, Triple H, and Chyna).[25] As a member of DX, Rude never wrestled, but stayed ringside during the group's matches. He once again left WWF after the Montreal Screwjob at Survivor Series. According to Bret Hart, Rude stayed in the locker room during Bret's confrontation with Vince McMahon, later calling Eric Bischoff and informing him what had happened was in fact real. As Rude was not signed to a full-time contract with WWF, and was instead performing on a "pay-per-appearance" basis, Rude was able to negotiate a deal with Bischoff and WCW, in part due to his anger over the Montreal Screwjob.[13][26]

Rude appeared on both WWF Raw is War and WCW Monday Nitro on November 17, 1997. A mustached Rude appeared on Nitro, which was live, and proceeded to criticize Shawn Michaels, DX, and the WWF, calling the company the "Titanic" (a reference to Titan Sports, as WWF's parent company was then known, as the "sinking ship").[1] An hour later on Raw (which had been taped six days earlier), Rude then appeared with the full beard he had been sporting during his return to the WWF.[1][27] Rude also appeared on ECW's Hardcore TV during that weekend (November 14–16 as the show was syndicated differently depending on the market). Rude was still making ECW appearances while in D-Generation X.

In WCW, Rude became a member of the nWo, managing his friend Curt Hennig.[10] When the nWo split, Hennig and Rude joined the NWO Wolfpac,[28] and they tried to motivate Konnan to defeat Goldberg, who was undefeated at the time. When Konnan was defeated by Goldberg, Rude and Hennig attacked him, later joining nWo Hollywood, the rivals of the Wolfpac. By late 1998, both Rude and Hennig were off WCW TV due to injuries. Hennig had an ongoing leg injury that year, and Rude was thought to have had testicular cancer which later turned out to be a spermatocele. Curt Hennig returned to the nWo from his injury at Starrcade 1998 without Rude, who was still unable to appear. Rude left the company in early 1999.[29]

Rude died on April 20, 1999, at the age of 40 when he suffered from heart failure. He was survived by his wife, Michelle, and their three children. An autopsy report showed he died from an overdose of "mixed medications." [30]

At the time of his death, Rude was in training for a return to the ring.[29]

In his autobiography, Bret Hart has stated that Rude was one of his closest friends and despite his portrayal of an arrogant womanizer, Rude was a devoted family man who never took his wedding ring off even during matches; covering it up with tape.

Rude, like many other wrestlers disliked working with the Ultimate Warrior, with whom he had a series of matches with in the early 90's and was known for being "stiff" with his opponents. During a match, Rude had Warrior in a hold and warned him that if he didn't ease up, he would "rip his head off and shove it up his ass".[citation needed]